Reese Witherspoon & Ryan Phillipe

Winner: Reese Witherspoon It was one of those Hollywood love stories that seemed almost too perfect: They met at her 21st birthday party, they were linked in the movie "Cruel Intentions," then they tied the knot in real life. Two children and a "Walk the Line" Oscar for her later, it was over for Reese and Ryan. She has continued to star in high-profile projects -- while having another high-profile Hollywood romance, this time with Jake Gyllenhaal -- and he has kept making respected, if not hugely profitable, films.

Winner: Reese Witherspoon It was one of those Hollywood love stories that seemed almost too perfect: They met at her 21st birthday party, they were linked in the movie "Cruel Intentions," then they tied the knot in real life. Two children and a "Walk the Line" Oscar for her later, it was over for Reese and Ryan. She has continued to star in high-profile projects -- while having another high-profile Hollywood romance, this time with Jake Gyllenhaal -- and he has kept making respected, if not hugely profitable, films. (WireImage)

Winner: Reese Witherspoon It was one of those Hollywood love stories that seemed almost too perfect: They met at her 21st birthday party, they were linked in the movie "Cruel Intentions," then they tied the knot in real life. Two children and a "Walk the Line" Oscar for her later, it was over for Reese and Ryan. She has continued to star in high-profile projects -- while having another high-profile Hollywood romance, this time with Jake Gyllenhaal -- and he has kept making respected, if not hugely profitable, films.WireImage